Q&A: What was the mistake that killed your last B2B sales deal?

Some mistakes I’ve made in which have lost us B2B sales over the years:

  1. Lack of follow up. Make sure you have a process in place to follow up on every deal. It’s really easy in a small company to lose track of these deals, but it’s even easier for big enterprise buyers to lose track of you! Especially early in the process.
  2. Not understanding that you’re selling a solution. You think you’re selling software, but they’re not buying software at the enterprise level. They’re buying a solution. This is REALLY hard if you’re a small co. who won’t be sending consultants on-site to help them implement, etc. But some things you can do which helpful:
    1. Offer product training via webinar on a regular basis
    2. Offer bespoke customer on-boarding (for an extra fee)
    3. Try and convey the ongoing relationship you’ll have with the customer, product roadmap, touch points with support, etc.
  3. Not building trust. It’s often said that enterprise customers are not paying with their own money. That’s true and it’s great, but that doesn’t mean nothing is being spent.

    In fact, what the internal buyer is doing is often more stressful for them than a founder buying a software product. The founder buys and if it doesn’t work they move on. The internal buyer buys and if it’s a disaster they lose their job.

Original reply: https://www.quora.com/What-was-the-mistake-that-killed-your-last-B2B-sales-deal/answer/Ian-Landsman?srid=XJ0


People go to conferences with the wrong mindset. They feel as though they have to get a lot of information out of it or make a lot of contacts. They need to justify the expense with volume.

For me, I only ever have one goal and that is to get one actionable item from the trip. It could be an idea or a connection. Either way, if I leave with one solid next step it easily pays for the cost of the conference.

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Travis Kalanick Interview

This is simply a beautiful interview. If you’re in business there’s no way you can’t love the clarity of his vision. The elegance of his presentation.

Grab a cup of coffee and enjoy.

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The Knife-Edge

You spend a lot of time as a bootstrapped software founder on a knife-edge.

How can I afford to start a business? Will the business succeed or fail? Will anyone buy my product?

Once you overcome these questions you need to start thinking about hiring. There are a lot of great reasons to start hiring early in the success of your software business. I waited way to long with UserScape to start hiring.

This post isn’t about all those reasons you’ve already heard about. To feed the growth, to get to the next level, to move faster, to build up sales, etc. This one is much more practical.

As you cross that line from barely making it to relatively profitable you’re in an extremely dangerous position. As a solo founder or even potentially in a partnership what happens if you get sick? If you have a serious family situation? If for some reason you can’t run the business for 6 months?

Not fun things to think about, but as you’ve probably left a good job and invested a lot of time and money to get this business going these are things you should think about. Having even just 1 great employee can make all the difference.

Even if they’re not a programmer and no work gets done on the product. Someone to answer the phone, do support, help sales, and keep the lights on can make all the difference between returning to a going concern and a dead husk.

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Here’s Why Devs Fail as Founders

I’m a big Seth Godin fan. You can see the signed #32 print of Purple Cow above. This print is probably my favorite bit of internet/tech swag.

Anyway, he wrote something tonight that really struck me as getting at the root of why so many software developers fail as founders. I’ve preached it for years, much of the earliest writing on this blog is about the topic. Yet, Seth being who he is is able to capture it more clearly than I ever have.

It’s pretty clear that the design of the egg carton isn’t going to change the flavor of the omelette.

Except, of course, it does.

As software developers we want the best tech to win. The best features. The right UI. Yet so often, almost aways in fact, those things are not what make or break a company. It’s your message, your pricing, the partnerships you make, the niche you target, a bit of marketing inspiration, website design, better docs, how the product makes you feel.

In short, the human element.

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Laravel Gurus 2

Laravel Gurus is a little labor of love site I run. It’s a simple listing of Laravel/PHP consultancies across the world. People kept asking me where to find a Laravel consultancy, now I just point them here.

Version 1 was built on top of Wufoo, which was kinda crazy.

For version 2, I rebuilt everything on Laravel 5.2. You can now request to be listed directly from the site (revolutionary!).

My favorite part of the site is the map. It’s just wonderful to see how Laravel is embraced across the world.

There’s currently 238 agencies, consultancies, and freelancers listed. If you’re not already listed make sure to get listed. If you are already listed you can now manage your listing. Use the password reset with the email address you originally signed up with.

Big thanks to all the Laravel community tools that make building this easy.

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The Hubris Bubble

There’s been a lot of talk about tech being in a bubble lately, making reference to the Internet bubble of 2000. I generally don’t agree with this, however, I do think we’ve reached a Hubris Bubble.

This tweet conversation really sums it up for me.

Screen Shot on 2016-01-28 at 08-19-56

In an environment focused on squeezing every last dollar out of every last visitor (can you say Growth Hacker?) it’s mind blowing that the Pied Piper of startups would think being on a show that reaches millions of people, that gives you 10 solid minutes of free airtime, that spins off thousands and thousands of blog posts, news items, and tweets would be considered a waste of time.

This is how far away from reality we’ve gotten. How far we’ve moved from focusing on building great profitable companies.

How the only thing investors want is to have their name associated with something “world changing”. Forget the idea of building a strong future for you, your employees, their families, their communities, the world at large.

It’s about the ego of millionaires (billionaires) finding that money isn’t all that glorious. They need to put their name on something so the world knows they existed. They’re not going to do the work of course. YOU should do the work and take the risk and ignore the giant marketing opportunities that any other business would kill for.


Yes, as a founder you should avoid distraction. An opportunity like that though isn’t distraction, it’s what you’re supposed to be doing.

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Overexposure to Excellence

One of the worst parts about running a business online is overexposure to excellence.

The world is a big place. If you’re on Twitter all day as so many of us are, you’re bombarded with excellence.

Competitors whose design is better, who have more features, who have better features.

Peers who are smarter.

People you follow with more followers, more access, more influence, more results.

Even for someone with a decade old business it can be discouraging. Worse, it can trick you into making bad decisions for your own business. Making you believe you must be everywhere at once, market on every channel, move forward on every feature.

The world is a big place and you only need to sell to a very small slice of it to be wildly successful.

The key is to not play their game, play your own game.

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Customer Success in SaaS

This quote on the latest Bootstrapped Web (a podcast I really enjoy!) by Jordan struck a nerve with me

Do you hire for the least important things or least impactful things like customer support and customer success. Or do you actually hire for the most strategic things like content marketing, email marketing.

I’m not trying to call Jordan out for an off hand comment on a podcast, but I do think this is a good jumping off point to discuss how I believe people should view customer support in SaaS. To me, customer success teams are the most important part of a SaaS business. There’s nothing more strategic than top notch support.

Without a great customer success team all the work of every other department is wasted. Customer Success is the glue that ties marketing and product development to revenue.

New customers are expensive to get, keeping existing ones is cheap and far far more profitable. This is doubly so in SaaS where you don’t get all the money up front, but generally must wait years to earn the majority of the customers lifetime value.

How SaaS causes this alignment between the customer and the developers best interest is one of its greatest strengths. To make this work though you have to realize the pressing importance of the customer success team. Great customer success hires generate revenue.

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The Product Business Cycle

This tweet from a developer at a local company got me thinking about the software product lifecycle.


Perhaps you can think of building a product this way, but the vast majority of products are businesses and you certainly can’t build a business this way.

My take on the iterative process of building a product business would be more like this:

Research → Ideas → Idea → Confirm → Design → Code → Launch → Customer → Customers → Support → Marketing → Customers → Tweak (Code?) → ReLaunch → Support → Marketing → Customers

in Post | 83 Words